N-alkylation of heterocyclic, aromatic amines

Details N-alkylation of heterocyclic, aromatic amines N-alkylation of heterocyclic, aromatic amines

1992-05-08

1994-02-01

Higel, Floyd D.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548110, 5483044, 5483551, 5483001, 5483731, 5483741, 548579, 564480, 502155, 502162, 502326, B01J 2346, C07D23354, C07D24922, C07D40302

Patent

active

052833410

ABSTRACT:
A process for producing a heterocyclic tertiary amine of the formula (III): ##STR1## wherein A is a nitrogen atom or C-R.sup.5, B is a nitrogen atom or C-R.sup.6, is a single bond or a double bond, and each of R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 which may be the same or different, is a hydrogen atom, an acyl group, a halogen atom, a cyano group, etc., provided that two of R.sup.1, R.sup.2, R.sup.3 and R.sup.4 may together form a 3-membered, 4-membered, 5-membered or 6-membered aliphatic ring, a heterocyclic rig or aromatic ring, and R.sup.7 is a C.sub.1-6 alkyl group which may be substituted, etc., which process comprises reacting a heterocyclic secondary amine of the formula (I): ##STR2## wherein A, B, , R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are as defined above, with an alkylating agent of the formula (II):

REFERENCES:
patent: 3223734 (1965-12-01), Fallstad et al.
patent: 3600413 (1971-08-01), Grimm
patent: 3708539 (1973-01-01), Fenton et al.
patent: 4105657 (1978-08-01), Dockner et al.
Patent Abstracts of Japan, vol. 2, No. 52, Apr. 14, 1978, & JP-A-53-009-725, Jan. 28, 1978, H. Hayamizu, et al., "Preparation of N-Alkylaromatic Amines".
Bulletin of the Chemical Society of Japan, vol. 50, No. 6, pp. 1510-1512, Jun. 1977, M. Hayashi, et al., "N-Alkylation Of Nitrogen Heterocyclic Compounds With Dialkyl Phosphites".
Journal of the American Chemical Society, vol. 101, No. 1, pp. 490-491, Jan. 17, 1979, S. E. Diamond, et al., "Reactions Of Aniline With Olefins Catalyzed by Group 8 Metal Complexes: N-Alkylation And Heterocycle Formation".

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